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WO1997038041A1 - Polymeres siloxane a greffage en forme d'etoile, poudres ceramiques enrobees avec lesdits polymeres et procede de fabrication de poudres ceramiques enrobees - Google Patents

Polymeres siloxane a greffage en forme d'etoile, poudres ceramiques enrobees avec lesdits polymeres et procede de fabrication de poudres ceramiques enrobees Download PDF

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Publication number
WO1997038041A1
WO1997038041A1 PCT/US1997/005179 US9705179W WO9738041A1 WO 1997038041 A1 WO1997038041 A1 WO 1997038041A1 US 9705179 W US9705179 W US 9705179W WO 9738041 A1 WO9738041 A1 WO 9738041A1
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Prior art keywords
ceramic powder
coated
ceramic
powder
siloxane
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Ceased
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PCT/US1997/005179
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WO1997038041B1 (fr
Inventor
Richard W. Brotzman, Jr.
John H. Aikens
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Solesense Inc
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Nanophase Technologies Corp
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Priority to AU24271/97A priority Critical patent/AU715859B2/en
Priority to EP97919963A priority patent/EP0891387B1/fr
Priority to JP9536259A priority patent/JP2000508684A/ja
Priority to CA002250962A priority patent/CA2250962C/fr
Priority to DE69729290T priority patent/DE69729290T2/de
Publication of WO1997038041A1 publication Critical patent/WO1997038041A1/fr
Publication of WO1997038041B1 publication Critical patent/WO1997038041B1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
    • C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
    • C04B35/626—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B
    • C04B35/628—Coating the powders or the macroscopic reinforcing agents
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    • C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
    • C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
    • C04B35/626—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B
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    • C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
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    • C04B35/626—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B
    • C04B35/628—Coating the powders or the macroscopic reinforcing agents
    • C04B35/62886—Coating the powders or the macroscopic reinforcing agents by wet chemical techniques
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    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
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    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/28—Compounds of silicon
    • C09C1/30—Silicic acid
    • C09C1/3081—Treatment with organo-silicon compounds
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    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/36—Compounds of titanium
    • C09C1/3607—Titanium dioxide
    • C09C1/3684—Treatment with organo-silicon compounds
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    • C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
    • C09C3/12—Treatment with organosilicon compounds
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
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    • C01P2004/80—Particles consisting of a mixture of two or more inorganic phases
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    • C01P2004/80—Particles consisting of a mixture of two or more inorganic phases
    • C01P2004/82—Particles consisting of a mixture of two or more inorganic phases two phases having the same anion, e.g. both oxidic phases
    • C01P2004/84—Particles consisting of a mixture of two or more inorganic phases two phases having the same anion, e.g. both oxidic phases one phase coated with the other
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    • C04B2235/00—Aspects relating to ceramic starting mixtures or sintered ceramic products
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    • C04B2235/30—Constituents and secondary phases not being of a fibrous nature
    • C04B2235/32—Metal oxides, mixed metal oxides, or oxide-forming salts thereof, e.g. carbonates, nitrates, (oxy)hydroxides, chlorides
    • C04B2235/3217—Aluminum oxide or oxide forming salts thereof, e.g. bauxite, alpha-alumina
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    • C04B2235/00—Aspects relating to ceramic starting mixtures or sintered ceramic products
    • C04B2235/02—Composition of constituents of the starting material or of secondary phases of the final product
    • C04B2235/30—Constituents and secondary phases not being of a fibrous nature
    • C04B2235/32—Metal oxides, mixed metal oxides, or oxide-forming salts thereof, e.g. carbonates, nitrates, (oxy)hydroxides, chlorides
    • C04B2235/3231—Refractory metal oxides, their mixed metal oxides, or oxide-forming salts thereof
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    • C04B2235/00—Aspects relating to ceramic starting mixtures or sintered ceramic products
    • C04B2235/02—Composition of constituents of the starting material or of secondary phases of the final product
    • C04B2235/30—Constituents and secondary phases not being of a fibrous nature
    • C04B2235/32—Metal oxides, mixed metal oxides, or oxide-forming salts thereof, e.g. carbonates, nitrates, (oxy)hydroxides, chlorides
    • C04B2235/327—Iron group oxides, their mixed metal oxides, or oxide-forming salts thereof
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    • C04B2235/30—Constituents and secondary phases not being of a fibrous nature
    • C04B2235/32—Metal oxides, mixed metal oxides, or oxide-forming salts thereof, e.g. carbonates, nitrates, (oxy)hydroxides, chlorides
    • C04B2235/3284—Zinc oxides, zincates, cadmium oxides, cadmiates, mercury oxides, mercurates or oxide forming salts thereof
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    • C04B2235/00—Aspects relating to ceramic starting mixtures or sintered ceramic products
    • C04B2235/02—Composition of constituents of the starting material or of secondary phases of the final product
    • C04B2235/30—Constituents and secondary phases not being of a fibrous nature
    • C04B2235/34—Non-metal oxides, non-metal mixed oxides, or salts thereof that form the non-metal oxides upon heating, e.g. carbonates, nitrates, (oxy)hydroxides, chlorides
    • C04B2235/3418—Silicon oxide, silicic acids or oxide forming salts thereof, e.g. silica sol, fused silica, silica fume, cristobalite, quartz or flint
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    • C04B2235/00—Aspects relating to ceramic starting mixtures or sintered ceramic products
    • C04B2235/02—Composition of constituents of the starting material or of secondary phases of the final product
    • C04B2235/30—Constituents and secondary phases not being of a fibrous nature
    • C04B2235/48—Organic compounds becoming part of a ceramic after heat treatment, e.g. carbonising phenol resins
    • C04B2235/483—Si-containing organic compounds, e.g. silicone resins, (poly)silanes, (poly)siloxanes or (poly)silazanes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
    • Y10T428/2991—Coated
    • Y10T428/2993—Silicic or refractory material containing [e.g., tungsten oxide, glass, cement, etc.]
    • Y10T428/2995—Silane, siloxane or silicone coating
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
    • Y10T428/2991—Coated
    • Y10T428/2998—Coated including synthetic resin or polymer

Definitions

  • This invention relates generally to ceramic powder coatings. More particularly, this invention relates to siloxane star-graft polymers for coating ceramic powders, thereby enabling the dispersion of such powders in oils, polymers and water.
  • a coating is required to enable the surface to be wetted by, or compatible with, organic materials such as solvents.
  • a coating is required to render anatase titama (T ⁇ 0 2 ) non-photoactive.
  • ceramic refers to metal oxides, including but not limited to titanium dioxide (T ⁇ 0 2 ; sometimes referred to as "titania") , alumina (Al 2 0 3 ) , zinc oxide (ZnO) , and iron oxides including ⁇ -Fe 2 0 3 (brown in color) , ⁇ -Fe 2 0 3 (red m color) and ferrous oxide (Fe 3 0 4 ; black in color; sometimes referred to as "magnetite”) , and nonmetal oxides, including but not limited to silicon dioxide (Si0 2 ; sometimes referred to as "silica”) .
  • Inorganic surfaces have been conventionally modified by absorption, ion exchange, and covalent bonding. Surface modification by absorption and ion exchange require the surface to have appropriate chemical characteristics. Reactions that enable covalent bonding to inorganic surfaces generally involve reactions on hydroxylic surfaces. Inorganic surfaces may also be coated by graft polymerization and encapsulation. Inorganic powders may be coated by the precipitation of powders in the presence of suspended powders or by spray drying of polymer solutions containing the powder. However, these conventional methods yield uneven coatings and the formation of coated agglomerates. Graft polymerization initiated by adsorbed species, or involving their copolymerization, favors uniform polymeric coatings.
  • the present siloxane star-graft polymer coatings are derived from the acid-catalyzed silicate sols discussed in Sol-Gel Science, C.J. Bunker and G.W. Scherer, Academic Press, 1990, Chapters 3 and 4.
  • Such acid-catalyzed silicate sols are fractal, silicon-based polymers, the structure of which is shown, m two-dimensions, in FIG. 1.
  • the present siloxane star-graft polymers employ this polymer morphology, in three dimensions, as a starting point, bonding to the fractal backbone specific moieties, thereby forming a fractal, star-graft copolymer using molecularly engineered inorganic surface/diluent interactions.
  • Inherent in the present method of preparing such siloxane star-graft polymers is the control of the fractal nature of the backbone by allowing only desired branching probabilities to occur. Such control is realized by selection of monomers with the desired functionality and reactivity.
  • Silicon-based polymers will be referred to herein using the following nomenclature:
  • w, x, y and z refer to the mole percent tetrafunctional, trifunctional, difunctional and monofunctional monomers, respectively, that are employed in synthesizing the sol.
  • the ratio of total moles water to total moles silicon (H 2 0/Si) is termed R, where R is a measure of the degree of polymer branching.
  • the present siloxane star-graft polymer coatings are formed by reacting specific monomers in solution to form a siloxane-based polymer.
  • the coating encapsulates the nanoparticle .
  • a coated ceramic powder comprises a plurality of ceramic particles and a siloxane star-graft coating polymer encapsulating at least a portion of the particles.
  • the coating polymer comprises:
  • the ceramic is Ti0 2 , A1 2 0 3 , ZnO, iron oxide or Si0 2 .
  • the iron oxide is ⁇ -Fe 2 0 3 , ⁇ -Fe 2 0 3 or Fe 3 0 4 .
  • the coated ceramic powder preferably further comprises Al +3 centers to introduce surface defects into the Ti0 2 powder, thereby rendering the coated Ti0 2 powder non- photoactive .
  • w is tetraethylorthosilicate
  • x is selected from the group consisting of ⁇ -glycidoxypropyltrimethoxysilane, n- hexyltrimethoxysilane, isobutyltrimethoxy- silane, ⁇ -methacryloxypropyltrimethoxysilane, n-octadecyltrimethoxysilane, and n-propyltri- methoxysilane
  • - y is selected from the group consisting of dicyclohexyldimethoxysilane, diethyldieth- oxysilane, dimethyldichlorosilane, dimethyl- diethoxysilane, dimethyldimethoxysilane, diphenyldiethoxysilane, diphenyldimethoxy- silane, di-n-hexyldichlorosilane, n-hexyl- methyldichlorosilane,
  • a method of preparing the above coated ceramic powder comprises the steps of : (a) polymerizing a tetrafunctional siloxane monomer and at least one of a trifunctional siloxane monomer, a difunctional siloxane monomer and a monofunctional siloxane monomer;
  • step (d) adding the siloxane polymer prepared in step (a) to the reaction vessel containing the shear mixed ceramic powder;
  • the ceramic is Ti0 2 , A1 2 0 3 , ZnO, Fe 2 0 3 or Si0 2 .
  • a further quantity of aluminum tri-sec-butoxide is optionally added to the reaction vessel in step (b) to introduce surface defects into the Ti0 2 powder, thereby rendering the coated Ti0 2 powder non-photoactive.
  • the tetrafunctional siloxane monomer is tetraethylorthosilicate
  • the trifunctional siloxane monomer is selected from the group consisting of ⁇ - glycidoxypropyltrimethoxysilane, n- hexyltrimethoxysilane, isobutyltrimethoxy- silane, ⁇ -methacryloxypropyltrimethoxysiiane , n-octadecyltrimethoxysilane, and n-propyltri- methoxysilane
  • the difunctional siloxane monomer is selected from the group consisting of dicyclohexyldimethoxysilane, diethyldiethoxysilane, dimethyldichlorosilane, dimethyldiethoxysilane, dimethyldimeth- oxysilane, diphenyldiethoxysilane, diphenyldi- methoxysilane, di-n
  • a siloxane star-graft polymer for coating and encapsulating ceramic particles comprises:
  • w, x, y and z are the mole percent tetrafunctional, trifunctional, difunctional and monofunctional monomeric units, respectively, and wherein w is at about 20-100 and x, y and z are about 0-30, 0-50 and 0-10, and at least one of x, y and z is greater than zero.
  • w is tetraethylorthosilicate
  • x is selected from the group consisting of ⁇ -glycidoxypropyltrimethoxysilane, n- hexyltrimethoxy ⁇ ilane, isobutyltrimethoxy- silane, ⁇ -methacryloxypropyltrimethoxysilane, n-octadecyltrimethoxysilane, and n-propyltri- methoxysilane
  • y is selected from the group consisting of dicyclohexyldimethoxysilane, diethyldieth- oxysilane, dimethyldichlorosilane, dimethyl- diethoxysilane, dimethyldimethoxysilane, diphenyldiethoxysilane, diphenyldimethoxy- silane, di-n-hexyldichlorosilane, n-hexyl- methyld
  • FIG. 1 is a schematic diagram of a fractal, silicon-based polymer, the structure of which is shown in two-dimensions .
  • w, x, y and z in the above silicon-based polymers have ranged from 20-100, 0- 30, 0-50 and 0-10, respectively.
  • Various combinations are employed to control the fractal nature of the siloxane backbone and its chemical nature, that is, the degree of thermodynamic compatibility with a specific diluent of the coating molecule.
  • the chemical identity of the groups may also be varied extensively.
  • R has been varied from 1 to 6, and the acid character of the reaction medium has been varied widely. Examples of monomers that may be incorporated in the coating are included, but not limited to, those set forth in Table 1
  • the product prepared by the above batch process contains approximately 15 weight percent (wt%) coating polymer.
  • reaction solvent such as, for example, anhydrous ethanoi, ethanoi and/or isopropanol
  • ASTB aluminum tri-sec-butoxide + approximately 500 ml isopropanol .
  • ASTB solution in a small stream via cannula by argon pressure displacement .
  • the addition of ASTB introduces Al *3 centered surface defects into the
  • Epoxy polymers - Si60, 20, 15, 5)/ tetraethylorthosilicate, - glycidoxypropyltrimethoxysilane, diphenyldimethoxysilane, trimethylethoxy ⁇ silane; R 1.12, ⁇ 60°C 1.5 hr.

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  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Silicon Polymers (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Glanulating (AREA)
  • Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
  • Oxygen, Ozone, And Oxides In General (AREA)
  • Inorganic Compounds Of Heavy Metals (AREA)
  • Compounds Of Alkaline-Earth Elements, Aluminum Or Rare-Earth Metals (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Compounds Of Iron (AREA)
  • Silicon Compounds (AREA)

Abstract

Poudre céramique enrobée comprenant plusieurs particules céramiques et un polymère d'enrobage siloxane avec greffage en forme d'étoile et enrobant au moins une partie des particules. Le polymère d'enrobage comprend Si (w, x, y, z), w, x, y et z étant respectivement des unités monomères tétrafonctionnelles, trifonctionnelles, bifonctionnelles et monofonctionnelles à pourcentage molaire, w étant d'environ 20 à 100, x d'environ 0 à 30, y d'environ 0 à 50 et z d'environ 0 à 10, et au moins une unité parmi w, x, y et z étant supérieure à zéro. Le procédé de fabrication d'une poudre céramique enrobée comprend les stades suivants: (a) polymérisation d'un monomère tétrafonctionnel du siloxane et d'au moins un monomère trifonctionnel, bifonctionnel et monofonctionnel du siloxane, (b) ajout d'une certaine quantité de poudre céramique dans la cuve à réaction, (c) mélangeage cisaillé de la poudre céramique pendant un laps de temps suffisant pour humecter de façon substantielle toute la surface de la poudre, (d) ajout du polymère du siloxane préparé au stade (a) dans la cuve à réaction contenant de la poudre mélangée avec cisaillement, (e) mélangeage cisaillé de la poudre céramique mélangée avec cisaillement et du polymère du siloxane pendant un laps de temps suffisant pour former une poudre céramique enrobée de polymère de siloxane et (f) séparation de la poudre céramique enrobée des composants résiduels dans la cuve à réaction.
PCT/US1997/005179 1996-04-04 1997-03-28 Polymeres siloxane a greffage en forme d'etoile, poudres ceramiques enrobees avec lesdits polymeres et procede de fabrication de poudres ceramiques enrobees Ceased WO1997038041A1 (fr)

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AU24271/97A AU715859B2 (en) 1996-04-04 1997-03-28 Siloxane star-graft polymers, ceramic powders coated therewith and method of preparing coated ceramic powders
EP97919963A EP0891387B1 (fr) 1996-04-04 1997-03-28 Polymeres siloxane a greffage en forme d'etoile, poudres ceramiques enrobees avec lesdits polymeres et procede de fabrication de poudres ceramiques enrobees
JP9536259A JP2000508684A (ja) 1996-04-04 1997-03-28 シロキサン星形グラフトポリマー、それによりコーティングされたセラミック粉末、及びコーティングされたセラミック粉末を調製する方法
CA002250962A CA2250962C (fr) 1996-04-04 1997-03-28 Polymeres siloxane a greffage en forme d'etoile, poudres ceramiques enrobees avec lesdits polymeres et procede de fabrication de poudres ceramiques enrobees
DE69729290T DE69729290T2 (de) 1996-04-04 1997-03-28 Sternförmig-gepfropfte siloxanpolymere, damit beschichtete keramikpulver, sowie ein verfahren zu deren herstellung

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US1483896P 1996-04-04 1996-04-04
US60/014,838 1996-04-04

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WO1997038041A1 true WO1997038041A1 (fr) 1997-10-16
WO1997038041B1 WO1997038041B1 (fr) 1997-11-06

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EP (1) EP0891387B1 (fr)
JP (2) JP2000508684A (fr)
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CA (1) CA2250962C (fr)
DE (1) DE69729290T2 (fr)
WO (1) WO1997038041A1 (fr)

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US6190731B1 (en) 1996-03-12 2001-02-20 Berhan Tecle Method for isolating ultrafine and fine particles and resulting particles
WO2003016217A1 (fr) 2001-08-16 2003-02-27 Essilor International Compagnie Generale D'optique Preparation de dispersions stables de nanoparticules metalliques, dispersions stables ainsi obtenues et compositions de revetement renfermant ces dispersions
EP1484361A1 (fr) * 2003-06-04 2004-12-08 E.I. Du Pont De Nemours And Company Matières polymères haute température comprenant des charges composites à résistance corona et procédés associés
US9139737B1 (en) 2011-11-21 2015-09-22 Nanophase Technologies Corporation Multifunctional coated powders and high solids dispersions
US10555892B1 (en) 2017-03-09 2020-02-11 Nanophase Technologies Corporation Functionalized siloxane or polysiloxane coated particles with enhanced light filtering properties
US10590278B2 (en) 2017-04-10 2020-03-17 Nanophase Technologies Corporation Coated powders having high photostability

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US6372077B1 (en) 1996-03-12 2002-04-16 Berhan Tecle Method for isolating ultrafine and fine particles and resulting particles
US5993967A (en) * 1997-03-28 1999-11-30 Nanophase Technologies Corporation Siloxane star-graft polymers, ceramic powders coated therewith and method of preparing coated ceramic powders
WO2003016217A1 (fr) 2001-08-16 2003-02-27 Essilor International Compagnie Generale D'optique Preparation de dispersions stables de nanoparticules metalliques, dispersions stables ainsi obtenues et compositions de revetement renfermant ces dispersions
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US9139737B1 (en) 2011-11-21 2015-09-22 Nanophase Technologies Corporation Multifunctional coated powders and high solids dispersions
US9657183B2 (en) 2011-11-21 2017-05-23 Nanophase Technologies Corporation Multifunctional coated powders and high solids dispersions
US10544316B2 (en) 2011-11-21 2020-01-28 Nanophase Technologies Corporation Multifunctional coated powders and high solids dispersions
US10555892B1 (en) 2017-03-09 2020-02-11 Nanophase Technologies Corporation Functionalized siloxane or polysiloxane coated particles with enhanced light filtering properties
US10590278B2 (en) 2017-04-10 2020-03-17 Nanophase Technologies Corporation Coated powders having high photostability
US11499054B2 (en) 2017-04-10 2022-11-15 Nanophase Technologies Corporation Coated powders having high photostability

Also Published As

Publication number Publication date
EP0891387B1 (fr) 2004-05-26
DE69729290D1 (de) 2004-07-01
DE69729290T2 (de) 2005-06-02
JP2000508684A (ja) 2000-07-11
US6033781A (en) 2000-03-07
AU2427197A (en) 1997-10-29
CA2250962A1 (fr) 1997-10-16
AU715859B2 (en) 2000-02-10
EP0891387A2 (fr) 1999-01-20
CA2250962C (fr) 2003-06-03
JP2007092063A (ja) 2007-04-12

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